Advice: How do I get this guy to sleep with me?

February 28, 2013|Anna Pulley, @annapulley | RedEye's sex columnist

So I met this guy about a month ago, and we dig each other. He's not looking for a relationship, and I'm not going to waste my energy trying to make him, so we're basically in the "friends with benefits" stage. The "benefits," however, only go so far. We've had several steamy makeout sessions in the car outside my house (with all the high school flashbacks included), but no sex. After one of these sessions, he told me he was having sex with someone else, and that it was a random, no-emotions arrangement. But we couldn't have sex because he felt guilty about having sex with two people at once. I should mention I'm polyamorous and do, in fact, sleep with more than one person. I would like him to be one of those people. My question is twofold: What the [bleep], is this dude stupid? And, I can't believe I'm saying this, how do I get this guy to sleep with me?--Benefit-less in Chicago

You know, there are hundreds of articles on how to get a woman to sleep with a man, but not the other way around. After exhaustive research, the only one I found simply said, "Take your shirt off," and since you've probably already rounded that base, I'm not going to repeat that sage advice (anymore than I already have just now). To answer your first question, there are a number of reasons for sleeping with only one person at a time, although "guilt" falls relatively low on that list, somewhere between "so I don't have to shave as often" and "so I don't have to choose between sex and my favorite Food Network programs." The obvious perks to monogamous sex are lower risk for STDs, familiarity, easier time-management, and having someone you trust to release the erotic asphyxiation noose before you lose all oxygen flow to your brain and die.

As uncouth as it may seem that your fella would rather be monog in a non-emotional, casual situation, it is ultimately his choice, and you have to respect it. If, however, you'd like to try to persuade him of your vagina's awesomeness (and I suggest this only as a temporary strategy), there are a few methods you can employ to help move things along.

One: If at first you don't succeed, try, try again. If you keep having hot and heavy makeout sessions, odds are eventually he'll want to take things further, unless he's Katy Perry, in which case, he kisses you and he likes it but his boyfriend probably minds.

Two: Try the opposite of what you've been doing. If you're the type to come on strong, then let him take the initiative. If you make out in cars, get thee to a dance floor, or any floor will do, really. Sometimes a change of pace/scenery/channel is all it takes to go from lip lock to bed rock--boot knock? Sock hop? (What? I like my sex to rhyme).

Three: Find someone who actually wants to sleep with you. Why put yourself through the frustration of a benefit-less friend when you don't have to? Is he under warranty? A friend-with-benefits arrangement has to be mutually beneficial to all parties involved. Give your blue labes a rest already and find that special someone(s) who will give you the deep dicking you so clearly deserve.